A fluorescent cyclotriveratrylene: synthesis, emission properties and acetylcholine recognition in water

Dumartin, Marie-Laurence; Givelet, Cécile; Meyrand, Pierre; Bibal, Brigitte; Gosse, Isabelle

doi:10.1039/b904590b

Cited by 26 publications

(17 citation statements)

References 22 publications

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“…The upfield shift and broadening of the signal of the Me 4 N + cation in the presence of 1 6– could result from the interaction of the former with the latter in the fast exchange limit on the 1 H NMR timescale. Indeed, anionic, water‐soluble, and luminescent CTB derivatives have been shown to bind ACh and other quaternary ammonium salts significantly at pH 7.2 (physiological medium), with binding constants ranging between 63 and 2300 m –1 . Therefore, inhibition of the templating effect of Me 4 N + at higher molar ratios could arise from the saturation of the concave binding sites of 1 6– by this quaternary ammonium cation.…”

Section: Resultsmentioning

confidence: 99%

Generation of Cryptophanes in Water by Disulfide Bridge Formation

Brégier¹,

Hudeček

Chaux³

et al. 2017

Eur J Org Chem

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International audienceCryptophanes are receptors consisting of two bridging concave cyclotribenzylene (CTB) subunits. The formation of cryptophanes in basic aqueous solutions (0.1 M MOD; M = Li, Na, K, and Cs) by disulfide bridge formation has been investigated. Two original CTBs, 1H(6) and 2H(6), derived from cyclotriphenolene through the introduction of mercaptomethyl and mercapto substituents, respectively, were synthesized. Cryptophane formation by slow oxygenation of 1(6-) was observed only in the presence of Me4N+ as template, which yielded the diastereomeric forms in a ratio of around 82:18. By contrast, the rigid CTB 2H(6) yielded a cryptophane stereoselectively without a template. Interestingly, air oxidation of a 1:1 mixture of 1(6-) and 2(6-) in the presence of Me4N+ (0.5-1 equiv./1(6-)) in 0.1 m LiOD led to the exclusive formation of the cryptophane complex [(1.1)(6-)superset of+NMe4], (2.2)(6-) being formed only in very minor amounts. No mixed species were detected in the reaction mixtures. The stabilities of the diastereomers of the protonated cryptophanes were calculated in the gas phase by DFT at the omega B97XD 6-311G(d,p) level of theory

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Section: Resultsmentioning

confidence: 99%

Generation of Cryptophanes in Water by Disulfide Bridge Formation

Brégier¹,

Hudeček

Chaux³

et al. 2017

Eur J Org Chem

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“…The concave-shaped cavity is responsible for the vast variety of supramolecular interactions with ionic and neutral small molecules [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 ]. Moreover, armed CTV can even coordinate large structures such as fullerenes, showing high flexibility towards different sizes of molecules [ 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Coordination Properties of a Water-Soluble Material by Cross-Linking Low Molecular Weight Polyethyleneimine with Armed Cyclotriveratrilene

Coghi

et al. 2021

Polymers

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In this study, a full organic and water-soluble material was synthesized by coupling low molecular weight polyethylenimine (PEI-800) with cyclotriveratrilene (CTV). The water-soluble cross-linked polymer contains hydrophobic holes with a high coordination capability towards different organic drug molecules. The coordinating capability towards hydrophilic drugs (doxorubicin, gatifloxacin and sinomenine) and hydrophobic drugs (camptothecin and celastrol) was analyzed in an aqueous medium by using NMR, UV-Vis and emission spectroscopies. The coordination of drug molecules with the armed CTV unit through hydrophobic interactions was observed. In particular, celastrol exhibited more ionic interactions with the PEI moiety of the hosting system. In the case of doxorubicin, the host–guest detachment was induced by the addition of ammonium chloride, suggesting that the intracellular environment can facilitate the release of the drug molecules.

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“…In this area, we recently reported the first fluorescent CTV that is able to recognize similarly ACh and Ch in aqueous media. 5 Its fluorescence, due to an intramolecular charge transfer between electron-withdrawing and donating groups, located on the aromatic cores of the CTV, is altered in the presence of the guest. The recognition is mainly due to p-cation interactions between the CTV aryl groups and the ammonium part of the guest.…”

Section: Introductionmentioning

confidence: 99%

C3-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition

Peyrard¹,

Chierici²,

Pinet³

et al. 2011

Org. Biomol. Chem.

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A new strategy to obtain fluorescent cyclotriveratrylene (CTV) probes is proposed. The key intermediate, a triiodo CTV, is prepared in 3 steps with 47% overall yield. The whole synthesis requires only one purification step. The potential of this triiodo CTV as an intermediate is illustrated through the synthesis of a fluorescent phosphorylated probe that is able to bind choline and acetylcholine in pseudo-physiological conditions, with selectivity towards choline. As a consequence, this intermediate should allow us to rapidly form a library of probes in order to highlight the most promising ones.

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A fluorescent cyclotriveratrylene: synthesis, emission properties and acetylcholine recognition in water

Cited by 26 publications

References 22 publications

Generation of Cryptophanes in Water by Disulfide Bridge Formation

Generation of Cryptophanes in Water by Disulfide Bridge Formation

Synthesis and Coordination Properties of a Water-Soluble Material by Cross-Linking Low Molecular Weight Polyethyleneimine with Armed Cyclotriveratrilene

C3-triiodocyclotriveratrylene as a key intermediate to fluorescent probes: application to selective choline recognition

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